Founded in 1840, Caldwell has been the seat of two counties. Before Burleson County organized in 1846, the community was the seat of Milam County. It was named for Mathew "Old Paint" Caldwell, noted frontiersman and a signer of the Texas Declaration of Independence.

In the 1850s, the town was a rendezvous for westbound immigrants, and it had one of the finest hotels on the Old San Antonio Road. Bed-and-breakfast accommodations are offered in historic buildings The town has been named the "Kolache Capital of Texas" by the Texas Legislature.

Caldwell is on the Presidential Corridor linking the George Bush Presidential Library and Museum in Bryan/College Station with the Lyndon Baines Johnson Library and Museum in Austin.

Caldwell lies on Texas 36, a segment of the Ports-to-Plains Highway connecting the state's heartland to coastal ports.

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